A driver state monitoring (DSM) system includes a wearable device main body worn by a user, a display unit, and an information collection unit that collects information related to a body state of the user. The DSM system includes a controller that, based on the collected information, senses a situation associated with the user's body state, and converts the collected information into a numerical value representing the body state of the user in context of the sensed situation. The controller further calculates a well-driving score for the user based on the numerical value that represents the body state of the user in context of the sensed situation; and controls at least one of the display unit or an image information output device to display the well-driving score and the numerical value that represents the body state of the user in context of the sensed situation.